Troubleshooting

Troubleshoot SMTP delivery

Resolve authentication, TLS, sender, relay, and filtering failures during an email test.

Email administrators7 min readUpdated July 17, 2026

Authentication failed

  • Confirm the username format required by the provider; many services require the full email address.
  • Replace the stored password if it was rotated or copied before the provider displayed its final value.
  • Confirm SMTP AUTH is permitted for the mailbox or application. Some providers require an app password or OAuth-based relay instead of the normal account password.

TLS or connection failed

  • Match port 587 with STARTTLS or port 465 with SSL/TLS unless the provider documents another combination.
  • Confirm the hostname is the provider’s SMTP hostname, not its webmail address.
  • Ask the provider or network administrator whether the server allows connections from the DMTG Tech service.

Sender rejected or relay denied

  • Use a From address the authenticated account is allowed to send as.
  • If the organization uses a connector or relay, confirm its accepted domains and source restrictions.
  • Check SPF, DKIM, and DMARC alignment with the organization’s email administrator.

The test says sent but no message arrived

  • Check spam, quarantine, transport rules, and the provider’s message trace.
  • Test a mailbox in the sender’s own organization and a separate external mailbox.
  • Allow a few minutes before repeating a test; repeated identical messages may be grouped or rate-limited.